European Journal of Organic Chemistry

Cover image for Vol. 2017 Issue 27

Early View (Online Version of Record published before inclusion in an issue)

Editor: Haymo Ross, Deputy Editor: Anne Nijs

Impact Factor: 2.834

ISI Journal Citation Reports © Ranking: 2016: 19/59 (Chemistry Organic)

Online ISSN: 1099-0690

Associated Title(s): Advanced Synthesis & Catalysis, Asian Journal of Organic Chemistry

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  1. 1 - 24
  1. Microreviews

    1. Radical Dioxygenation

      Recent Advances in Radical Dioxygenation of Olefins

      Raghunath Bag, Pinaki Bhusan De, Sourav Pradhan and Tharmalingam Punniyamurthy

      Version of Record online: 25 JUL 2017 | DOI: 10.1002/ejoc.201700512

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      An overview of recent developments in the vicinal dioxygenation of olefins by radical approaches is presented.

    2. Spirocycles

      Design and Synthesis of Spirocycles

      Sambasivarao Kotha, Nageswara Rao Panguluri and Rashid Ali

      Version of Record online: 24 JUL 2017 | DOI: 10.1002/ejoc.201700439

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      In this personal account, a variety of spirocycles were constructed by sequential use of metathesis and cycloaddition reactions along with different name reactions such as Claisen rearrangement (CR), Grignard addition, Fischer indolization (FI), Suzuki–Miyaura (SM) cross-coupling and the retro-Diels–Alder (rDA) reaction as key steps.

  2. Front Cover

    1. You have free access to this content
      Front Cover: Homogeneous Catalysis by Manganese-Based Pincer Complexes (Eur. J. Org. Chem. /2017)

      Marcel Garbe, Kathrin Junge and Matthias Beller

      Version of Record online: 24 JUL 2017 | DOI: 10.1002/ejoc.201701015

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      The cover picture shows the opening of a new chapter in the field of pincer and pincer-type complexes: “Manganese Pincer Complexes”. After ruthenium, iridium, and iron-based pincer-type complexes have been established as state-of-the-art catalysts for (de)hydrogenation reactions in the past decade, manganese pincer complexes have most recently been successfully applied in related transformations. Details on their recent progress in (de)hydrogenation and transfer (de)hydrogenation as well as in C–C and C–X bond-forming reactions are presented in the Microreview by M. Beller et al. on page -- ff (https://doi.org/10.1002/ejoc.201700376).

  3. Full Papers

    1. Organoboron Luminescence

      Design and Luminescence Chromism of Fused Boron Complexes Having Constant Emission Efficiencies in Solution and in the Amorphous and Crystalline States

      Kazumasa Suenaga, Kazuo Tanaka and Yoshiki Chujo

      Version of Record online: 20 JUL 2017 | DOI: 10.1002/ejoc.201700704

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      Novel boron complexes were designed and synthesized for realizing constant emission during phase transitions. The synthesized complexes show bright emission in various phases. Additionally, the luminescence color changes drastically during phase transition. We also found that diverse luminescence colors were obtained for each polymorph and for different substituents.

  4. Microreviews

    1. Organocatalysis

      Organocatalytic Asymmetric Synthesis of Tetrahydrothiophenes and Tetrahydrothiopyrans

      Buddhadeb Mondal, Shiny Nandi and Subhas Chandra Pan

      Version of Record online: 19 JUL 2017 | DOI: 10.1002/ejoc.201700503

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      This review summarizes the recent developments in the organocatalytic asymmetric synthesis of tetrahydrothiophenes and tetrahydrothiopyrans. A variety of sulfur-containing compounds have been employed for their preparation.

  5. Front Cover

    1. You have free access to this content
      Front Cover: Highly Regio- and Enantioselective γ-Alkylation of Linear α,β-Unsaturated Aldehydes (Eur. J. Org. Chem. /2017)

      Mahesh S. Kutwal and Chandrakumar Appayee

      Version of Record online: 19 JUL 2017 | DOI: 10.1002/ejoc.201700979

      Thumbnail image of graphical abstract

      The cover picture shows a natural environment where green leaves are growing in the presence of sun light, which is also responsible for the dried leaves falling onto the ground. Similarly, the chiral secondary amine not only catalyzes γ-alkylation reactions to form the R-isomers (major) but also destroys the corresponding S-isomers (minor). This in situ kinetic resolution contributes to the enantioenrichment of the γ-alkylated products along with the actual catalytic alkylation reaction. Details are discussed in the Communication by M. S. Kutwal and C. Appayee on page -- ff (https://doi.org/10.1002/ejoc.201700645).

  6. Full Papers

    1. Reaction Quantification

      Rearrangement in Stereoretentive Syntheses of Menthyl Chloride from Menthol: Insight into Competing Reaction Pathways through Component Quantification Analysis

      Lukas Hintermann and Kit Ming Wong

      Version of Record online: 17 JUL 2017 | DOI: 10.1002/ejoc.201700677

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      The surprising retention of configuration and absence of rearrangement in the synthesis of menthyl chloride from menthol has long been taken for granted. Reaction component quantification by means of NMR methods has now revealed a colorful diversity of reaction products. What once was termed “menthyl chloride” may often enough have been a complex assortment.

  7. Communications

    1. Esterification

      Zinc-Catalyzed Esterification of N-β-Hydroxyethylamides: Removal of Directing Groups under Mild Conditions

      Yuji Nishii, Takahiro Hirai, Sarah Fernandez, Paul Knochel and Kazushi Mashima

      Version of Record online: 12 JUL 2017 | DOI: 10.1002/ejoc.201700748

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      Amide-bond cleavage: Zinc-catalyzed esterification of unactivated tertiary amides is achieved with the assistance of intramolecular acyl rearrangement. This reaction can be applied to the one-pot removal of various amide-based directing groups under mild reaction conditions by using an epoxide as an external source of the N-β-hydroxy group.

  8. Full Papers

    1. Direct Sulfonamidation

      Direct Sulfonamidation of Primary and Secondary Benzylic Alcohols Catalyzed by a Boronic Acid/Oxalic Acid System

      Tristan Verdelet, Robert M. Ward and Dennis G. Hall

      Version of Record online: 10 JUL 2017 | DOI: 10.1002/ejoc.201700621

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      A catalytic method was developed for the direct transformation of primary and secondary benzylic alcohols into various sulfonamide products using a mixture of 2,3,4,5-tetrafluorophenylboronic acid and oxalic acid as a co-catalytic system under mild conditions. The gram-scalable reaction affords acceptable to excellent yields of products using relatively benign starting materials.

    2. Delayed Fluorescence

      Blue-to-Green Delayed Fluorescence of 2-Aminoisophthalic Acid Diesters Dispersed in Polymer Film

      Masaki Shimizu and Masaki Nakatani

      Version of Record online: 10 JUL 2017 | DOI: 10.1002/ejoc.201700695

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      We report the luminescent properties of 2-aminoisophthalic acid diesters, which show aggregation-induced (enhanced) emission and delayed fluorescence. The emergence of delayed fluorescence is ascribed to the small overlap between the HOMO and LUMO.

    3. Chemoselective Hydrosilylation

      A Mild and Chemoselective Hydrosilylation of α-Keto Amides by Using a Cs2CO3/PMHS/2-MeTHF System

      Govindharaj Kumar, Alagesan Muthukumar and Govindasamy Sekar

      Version of Record online: 10 JUL 2017 | DOI: 10.1002/ejoc.201700374

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      A Cs2CO3-catalyzed chemoselective hydrosilylation of α-keto amides to give structurally important mandelamides has been developed by using polymethylhydrosiloxane (PMHS) as the hydride source in 2-methyltetrahydrofuran (2-MeTHF), an eco-friendly green solvent. A mechanistic study reveals the base-catalyzed degradation of PMHS forms MeSiH3, the active species for the hydrosilylation process.

    4. Spiro Compounds

      Synthesis of 6-Azaspiro[4.3]alkanes: Innovative Scaffolds for Drug Discovery

      Bohdan A. Chalyk, Andrei A. Isakov, Maryna V. Butko, Kateryna V. Hrebeniuk, Olena V. Savych, Olexandr V. Kucher, Konstantin S. Gavrilenko, Tetiana V. Druzhenko, Vladimir S. Yarmolchuk, Sergey Zozulya and Pavel K. Mykhailiuk

      Version of Record online: 5 JUL 2017 | DOI: 10.1002/ejoc.201700536

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      New spirocyclic scaffolds for drug discovery have been synthesized in only two steps from common four-membered-ring ketones.

  9. Microreviews

    1. Heteroatomic Heck Reaction

      Heck-Like Reactions Involving Heteroatomic Electrophiles

      Bojan Vulovic and Donald A. Watson

      Version of Record online: 5 JUL 2017 | DOI: 10.1002/ejoc.201700485

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      Heck reaction goes heteroatomic: The functionalization of alkenes through Heck-like reactions is discussed. This microreview highlights the early developments in the field leading to heteroatomic Heck reactions (silyl-Heck, boryl-Heck and aza-Heck), current state of the area, as well as that of a few related processes.

  10. Front Cover

    1. You have free access to this content
      Front Cover: Gram-Negative Extremophile Lipopolysaccharides: Promising Source of Inspiration for a New Generation of Endotoxin Antagonists (Eur. J. Org. Chem. /2017)

      Flaviana Di Lorenzo, Jean-Marc Billod, Sonsoles Martín-Santamaría, Alba Silipo and Antonio Molinaro

      Version of Record online: 4 JUL 2017 | DOI: 10.1002/ejoc.201700919

      Thumbnail image of graphical abstract

      The cover picture shows the promising future perspective of the pluripotential use of lipopolysaccharides isolated from Gram-negative Extremophiles in several biomedical and biotechnological fields. It underlines the importance and modernity of the work in a scenario in which natural compounds are a source of inspiration for new drugs. In particular, lipopolysaccharides from extremophiles are a well-suited source to find and develop ad-hoc synthesized endotoxin antagonists. Details are presented in the Microreview by A. Silipo et al. on page -- ff (https://doi.org/10.1002/ejoc.201700113).

  11. Microreviews

    1. Heterocycles from Organosilanes

      Synthesis of O- and N-Heterocycles by Silyl-Prins Cyclization of Allylsilanes

      Carlos Díez-Poza and Asunción Barbero

      Version of Record online: 3 JUL 2017 | DOI: 10.1002/ejoc.201700644

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      Prins cyclization has emerged as one of the most powerful protocols for the efficient construction of heterocycles. The use of electron-rich allylsilanes as alkene derivatives has important advantages over the general method. We provide an overview of the synthesis of different-sized oxa- and azacycles by silyl-Prins cyclization, focusing on the factors that influence the outcome of the process.

    2. C–H Functionalization

      Recent Applications of Rh- and Pd-Catalyzed C(sp3)–H Functionalization in Natural Product Total Synthesis

      Patrick B. Brady and Vikram Bhat

      Version of Record online: 26 JUN 2017 | DOI: 10.1002/ejoc.201700641

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      Functionalizing C(sp3)–H bonds is now easier than ever. However, in complex settings, achieving predictable reactivity and regio- and stereocontrol remains challenging. This Microreview takes a critical look at recent syntheses of natural products that have utilized the strategic implementation of Rh- and Pd-catalyzed C(sp3)–H functionalizations in a wide range of situations.

    3. Base-Metal Catalysis

      Homogeneous Catalysis by Manganese-Based Pincer Complexes

      Marcel Garbe, Kathrin Junge and Matthias Beller

      Version of Record online: 26 JUN 2017 | DOI: 10.1002/ejoc.201700376

      Thumbnail image of graphical abstract

      We focus here on the development and synthesis of manganese-based pincer-type catalysts and on recent progress in their application. As well as for hydrogenations, we describe their utilisation for dehydrogenation, hydrosilylation, hydroboration and transfer (de)hydrogenation reactions. Additionally, the usage of manganese-based pincer complexes for C–C, C–N and C–O bond transformations is highlighted.

  12. Communications

    1. Organocatalysis

      Highly Regio- and Enantioselective γ-Alkylation of Linear α,β-Unsaturated Aldehydes

      Mahesh S. Kutwal and Chandrakumar Appayee

      Version of Record online: 23 JUN 2017 | DOI: 10.1002/ejoc.201700645

      Thumbnail image of graphical abstract

      Perfect regioselectivity is achieved in the γ-alkylation of linear α,β-unsaturated aldehydes in the presence of trifluoroethanol (TFE). Furthermore, in situ kinetic resolution is demonstrated for enantioenrichment of the γ-alkylated products. Together, the activation of electrophiles by TFE and in situ kinetic resolution allow excellent selectivity in dienamine catalysis to be realized.

  13. Microreviews

    1. Organocatalysis

      Asymmetric Supramolecular Organocatalysis: A Complementary Upgrade to Organocatalysis

      Kengadarane Anebouselvy, Kodambahalli S. Shruthi and Dhevalapally B. Ramachary

      Version of Record online: 21 JUN 2017 | DOI: 10.1002/ejoc.201700611

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      Asymmetric supramolecular organocatalysis emerges from many interactions between substrates and catalysts: namely, substrate–catalyst, catalyst–catalyst and substrate–substrate interactions. Here the importance and applications of these interactions in governing both the reactivity and the selectivity of asymmetric organocatalytic reactions as a result of stable pre-transition states are shown.

  14. Full Papers

    1. Chemoselective Homocoupling | Very Important Paper

      2,2′-Homocoupled Azine N,N′-Dioxides or Azine N-Oxides: CDC- or SNAr-Controlled Chemoselectivity

      Abadh Kishor Jha and Nidhi Jain

      Version of Record online: 5 JUN 2017 | DOI: 10.1002/ejoc.201700504

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      Unprecedented copper acetate catalysed and copper-free homocoupling reactions of 2-phenylpyridine N-oxides to yield N,N′-dioxides or N-monoxides in the presence of LiOtBu is reported. The chemoselectivity is governed by oxidative cross-dehydrogenative coupling and SNAr pathways, respectively.

  15. Microreviews

    1. Isotopic Labellings

      Modern Aspects of Isotopic Labellings in Terpene Biosynthesis

      Jeroen S. Dickschat

      Version of Record online: 31 MAY 2017 | DOI: 10.1002/ejoc.201700482

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      This review summarises the results of recent mechanistic investigations on enzymes involved in the biosynthesis of terpene precursors and on terpene cyclases by isotopic labelling experiments. The accumulated knowledge from these experiments is discussed against the background of insights obtained by quantum chemical calculations.

    2. Vinylindole Cycloadditions

      2- and 3-Vinylindoles as 4π Components in Cycloaddition Reactions

      Elisabetta Rossi, Giorgio Abbiati and Valentina Pirovano

      Version of Record online: 24 MAY 2017 | DOI: 10.1002/ejoc.201700120

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      2-Vinylindoles and 3-vinylindoles participate as 4π components mainly in [4+2] cycloaddition reactions. Reactions with activated dienophiles occur under Lewis-acid catalysis or organocatalysis. Simple π-systems such as allenes participate as dienophiles under gold activation conditions.

    3. Carbene Ligands with Tethers

      Dealing at Arm's Length: Catalysis with N-Heterocyclic Carbene Ligands Bearing Anionic Tethers

      Felix Pape and Johannes F. Teichert

      Version of Record online: 18 MAY 2017 | DOI: 10.1002/ejoc.201700124

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      An overview of the applications of bidentate N-heterocyclic carbenes (NHCs) bearing anionic heteroatom-based tethers in catalysis is presented.

    4. Extremophile LPS

      Gram-Negative Extremophile Lipopolysaccharides: Promising Source of Inspiration for a New Generation of Endotoxin Antagonists

      Flaviana Di Lorenzo, Jean-Marc Billod, Sonsoles Martín-Santamaría, Alba Silipo and Antonio Molinaro

      Version of Record online: 5 MAY 2017 | DOI: 10.1002/ejoc.201700113

      Thumbnail image of graphical abstract

      Extremophile Gram-negative bacterial lipopolysaccharides (LPSs) offer promising opportunities for a variety of biomedical and therapeutic applications. This review gives an overview on the chemical peculiarities of extremophile LPSs, providing the most promising results relating to their bioactivity. We discuss their pharmacological potential from the perspective of drug synthesis and development.

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